About This Role
Owning the overall relationship and driving revenue growth within a book of Cornerstone's largest and most complex enterprise clients is the core of this quota-carrying role. It combines deep account stewardship with an active hunting mindset, proactively identifying and closing new opportunities within existing accounts, not just managing renewals. The successful candidate will partner closely with Sales leadership, Customer Excellence, Customer Engagement, and Customer Support, while serving as the client's primary strategic, commercial, and executive relationship owner.
Responsibilities
- Own a book of strategic enterprise accounts, carrying a quota split approximately 85% expansion/cross-sell and 15% net-new development
- Own and cultivate C-level relationships (CHRO, CFO, CIO, etc.) as the primary trusted advisor and executive escalation point
- Hunt for whitespace within accounts - new business units, subsidiaries, or use cases not yet leveraging Cornerstone
- Expand Cornerstone's footprint across products (learning, performance, talent acquisition, AI-driven workforce solutions)
- Build and execute strategic account plans mapping org structure, executive stakeholders, budget cycles, and competitive exposure
- Drive and defend renewals, protecting and growing ARR
- Lead discovery workshops and executive business reviews that position Cornerstone against competitors
- Manage and forecast a pipeline of expansion and net-new opportunities across Commit, Probable, and Upside stages
- Maintain account intelligence - org charts, sponsor mapping, competitive landscape, renewal timing - to inform strategy and forecasting
- Travel as needed for in-person executive engagement, including QBRs, briefings, and on-site strategy sessions
Requirements
- 5+ years in strategic account management or enterprise sales, with a quota track record spanning both expansion and new business
- Demonstrated success building and owning C-level relationships, not just practitioner-level ones
- Proven success hunting new opportunities within an existing client base
- Ability to build and execute account plans for complex, matrixed organizations
- A consultative approach - diagnosing business needs and mapping them to multi-product solutions
- Strong forecasting discipline in a metrics-driven environment
- Excellent discovery, negotiation, and closing skills
- Willingness to travel as needed for executive relationship-building and on-site engagement
Nice to have:
- Experience selling into large, matrixed enterprises (healthcare, financial services, retail, or similar)
- Familiarity with AI-driven workforce/talent solutions and the competitive landscape (Workday, SAP Success Factors, Docebo, Service Now)
